Upper Matecumbe Key Travel Guide

Tourist Guide

Islamorada showing a beach bar
Islamorada which includes a beach
Islamorada
Islamorada showing mangroves, a marina and general coastal views
Islamorada showing a sandy beach, tropical scenes and general coastal views
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is 3.673.620 ₫ per night from 30 Nov to 1 Dec
3.673.620 ₫
5.616.445 ₫ total
30 Nov - 1 Dec
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,582 reviews)
Beautiful resort with lots of included activities & water sports. Friendly staff. Clean rooms.

Reviewed on 17 Nov 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is 6.830.348 ₫ per night from 30 Nov to 1 Dec
6.830.348 ₫
9.464.251 ₫ total
30 Nov - 1 Dec
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,271 reviews)
Nice place

Reviewed on 22 Nov 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is 4.076.452 ₫ per night from 30 Nov to 1 Dec
4.076.452 ₫
6.336.581 ₫ total
30 Nov - 1 Dec
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,268 reviews)
Loved the resort

Reviewed on 21 Nov 2025

Amara Cay Resort
See all 2,841 properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (572 reviews)
Beautiful oceanfront room, renovated, clean. Deducted a star because the blinds in the bedroom (parking lot side) were not sufficient to darken the room at night. Needs blackout curtains!

Reviewed on 19 Nov 2025

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
9.6/10 Exceptional! (68 reviews)
i like the fact that there's beach area but it was difficult to walk in an out of it due to the rocks. The pool filter could have been cleaned during our stay as there was multiple days of debris caught in the drain trap. would have enjoyed more dining options. Room was available before check in ...

Reviewed on 27 Oct 2025

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (112 reviews)
Yes everything was clean and neat , staff very helpful and friendly

Reviewed on 16 Nov 2025

Treasure Harbor
See all properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.
History of Diving Museum

History of Diving Museum

You can spend an afternoon browsing the exhibits at History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.

History of Diving Museum
Hurricane Monument which includes outdoor art and a monument

Hurricane Monument

3/5(2 reviews)

Learn about the local history of Islamorada when you take a trip to Hurricane Monument. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Hurricane Monument

Bud n' Mary's Dive Center

4.5/5(3 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.

Bud n' Mary's Dive Center

Islamorada Brewery & Distillery

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

Islamorada Brewery & Distillery

MoradaWay Arts & Cultural District

You can spend time browsing the exhibits at MoradaWay Arts & Cultural District during your travels in Islamorada.

MoradaWay Arts & Cultural District